Literature DB >> 21200554

Dichlorido(3,5-dimethyl-1H-pyrazole)[(3,5-dimethyl-1H-pyrazol-1-yl)(o-tol-yl)methanone]palladium(II).

Simphiwe M Nelana1, Gert J Kruger, James Darkwa.   

Abstract

In the title compound, [PdCl(2)(C(5)H(8)N(2))(C(12)H(12)N(2)O)], the Pd atom adopts a slightly distorted trans-PdCl(2)N(2) square-planar arrangement. The different Pd-N bond lengths can be related to the the electron-withdrawing effect of the o-toluoyl group on the substituted pyrazole ligand. The complex crystallizes as centrosymmetric hydrogen-bonded dimers through N-H⋯Cl linkages.

Entities:  

Year:  2007        PMID： 21200554      PMCID： PMC2915136          DOI： 10.1107/S1600536807066627

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Mukherjee (2000 ▶); Komeda et al. (2000 ▶); Li et al. (2002 ▶); Guzei et al. (2003 ▶); Guzei et al. (2005 ▶); Ojwach et al. (2005 ▶); Spencer et al. (2006 ▶); Allen (2002 ▶).

Experimental

Crystal data

[PdCl2(C5H8N2)(C12H12N2O)] M = 487.70 Orthorhombic, a = 15.908 (3) Å b = 15.479 (3) Å c = 16.602 (3) Å V = 4088.0 (12) Å3 Z = 8 Mo Kα radiation μ = 1.18 mm−1 T = 293 (2) K 0.32 × 0.28 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.703, T max = 0.843 43509 measured reflections 4023 independent reflections 2686 reflections with I > 2σ(I) R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.114 S = 1.08 4023 reflections 240 parameters H-atom parameters constrained Δρmax = 1.09 e Å−3 Δρmin = −0.49 e Å−3 Data collection: SMART-NT (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2008 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066627/hb2672sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066627/hb2672Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[PdCl2(C5H8N2)(C12H12N2O)]F000 = 1968
Mr = 487.70Dx = 1.585 Mg m−3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2686 reflections
a = 15.908 (3) Åθ = 2.2–26.0º
b = 15.479 (3) ŵ = 1.18 mm−1
c = 16.602 (3) ÅT = 293 (2) K
V = 4088.0 (12) Å3Block, yellow
Z = 80.32 × 0.28 × 0.15 mm
Bruker SMART CCD diffractometer4023 independent reflections
Radiation source: fine-focus sealed tube2686 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.056
T = 293(2) Kθmax = 26.0º
φ and ω scansθmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −19→19
Tmin = 0.703, Tmax = 0.843k = −18→19
43509 measured reflectionsl = −20→20
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.114  w = 1/[σ2(Fo2) + (0.0425P)2 + 9.9045P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4023 reflectionsΔρmax = 1.09 e Å−3
240 parametersΔρmin = −0.49 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.Atoms 'Deviations (Å)' Pd1 - 0.0116 (12) Cl1 - 0.0684 (12) Cl2 - 0.0665 (12) N11 0.0754 (17) N21 0.0711 (16)Atoms 'Deviations (Å)' N11 - 0.0012 (32) N12 0.0016 (33) C11 - 0.0010 (51) C12 - 0.0021 (49) C13 - 0.0038 (56) C14 0.0023 (42) C15 0.0042 (45)Atoms 'Deviations (Å)' N21 0.0327 (35) N22 - 0.0225 (38) C21 - 0.0159 (65) C22 0.0319 (54) C23 0.0057 (55) C24 - 0.0040 (49) C25 - 0.0279 (46)Atoms 'Deviations (Å)' C32 0.0353 (49) C31 0.0478 (44) C33 - 0.0055 (54) C34 - 0.0356 (52) C35 - 0.0064 (49) C36 0.0160 (51) C37 0.0075 (42) C26 - 0.0592 (38)'Plane 1' 'Plane 2' 'Interplanar Angle (°)' Square 'Ring 1' 86.66 (12) Square 'Ring 2' 68.13 (14) 'Ring 2' 'Ring 3' 55.98 (25)
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
C110.1260 (3)−0.2107 (3)0.4805 (3)0.0544 (13)
C120.1495 (4)−0.2290 (3)0.4037 (4)0.0588 (14)
H120.1646−0.28290.38360.071*
C130.1468 (4)−0.1521 (3)0.3608 (3)0.0551 (13)
C140.1168 (4)−0.2659 (4)0.5543 (4)0.087 (2)
H14A0.1677−0.29770.56310.130*
H14B0.0709−0.30540.54700.130*
H14C0.1057−0.22970.60010.130*
C150.1668 (5)−0.1341 (4)0.2743 (4)0.095 (2)
H15A0.1195−0.10670.24910.142*
H15B0.1791−0.18740.24720.142*
H15C0.2148−0.09660.27120.142*
C210.1020 (4)0.3084 (3)0.3533 (4)0.0726 (18)
C220.1203 (4)0.3102 (4)0.4313 (4)0.0668 (16)
H220.12990.35930.46230.080*
C230.1226 (4)0.2247 (3)0.4582 (3)0.0580 (14)
C240.0921 (6)0.3799 (4)0.2929 (5)0.115 (3)
H24A0.03380.39520.28860.173*
H24B0.11220.36080.24140.173*
H24C0.12380.42930.31000.173*
C250.1364 (5)0.1919 (4)0.5424 (4)0.095 (2)
H25A0.08500.16760.56260.142*
H25B0.15360.23880.57640.142*
H25C0.17930.14830.54190.142*
C260.0658 (4)0.1895 (4)0.2552 (3)0.0679 (16)
C320.2068 (4)0.1314 (4)0.2339 (4)0.0711 (17)
H320.22480.16550.27670.085*
C310.1223 (3)0.1290 (3)0.2129 (3)0.0495 (12)
C330.2646 (4)0.0820 (5)0.1902 (4)0.086 (2)
H330.32130.08290.20380.103*
C340.2379 (5)0.0334 (5)0.1288 (4)0.085 (2)
H340.27630.00120.09920.102*
C350.1495 (5)0.0305 (4)0.1079 (3)0.0738 (18)
H350.1312−0.00470.06590.089*
C360.0945 (4)0.0783 (4)0.1488 (3)0.0687 (17)
C370.0019 (5)0.0762 (5)0.1242 (4)0.093 (2)
H37B−0.01050.12540.09100.140*
H37C−0.03280.07760.17150.140*
H37A−0.00920.02420.09450.140*
N110.1224 (3)−0.0881 (3)0.4099 (2)0.0491 (10)
N120.1103 (3)−0.1256 (3)0.4824 (2)0.0521 (10)
H12A0.0943−0.09820.52480.062*
N210.1115 (2)0.1715 (2)0.3970 (2)0.0425 (9)
N220.0961 (3)0.2227 (3)0.3322 (3)0.0650 (13)
O10.0029 (4)0.2206 (3)0.2275 (3)0.1102 (19)
Cl10.25848 (9)0.04521 (9)0.42155 (10)0.0660 (4)
Cl2−0.02466 (9)0.02924 (9)0.36848 (9)0.0614 (4)
Pd10.11619 (2)0.03965 (2)0.39821 (2)0.04292 (14)
U11U22U33U12U13U23
C110.058 (3)0.038 (3)0.068 (3)0.002 (2)−0.001 (3)0.012 (2)
C120.064 (3)0.033 (3)0.080 (4)−0.004 (2)0.005 (3)−0.006 (3)
C130.070 (4)0.041 (3)0.054 (3)0.002 (3)0.014 (3)−0.009 (2)
C140.110 (6)0.063 (4)0.088 (5)0.006 (4)0.000 (4)0.026 (4)
C150.156 (7)0.071 (4)0.058 (4)−0.007 (5)0.025 (4)−0.009 (3)
C210.106 (5)0.037 (3)0.074 (4)0.011 (3)0.004 (4)0.001 (3)
C220.082 (4)0.046 (3)0.072 (4)0.003 (3)−0.001 (3)−0.022 (3)
C230.077 (4)0.043 (3)0.053 (3)0.008 (3)−0.002 (3)−0.011 (2)
C240.182 (9)0.053 (4)0.111 (6)0.023 (5)0.007 (6)0.022 (4)
C250.162 (8)0.072 (4)0.051 (4)0.014 (5)−0.011 (4)−0.012 (3)
C260.090 (5)0.057 (4)0.056 (3)0.022 (3)−0.004 (3)0.006 (3)
C320.078 (4)0.082 (4)0.054 (3)−0.003 (4)0.002 (3)0.011 (3)
C310.066 (3)0.043 (3)0.040 (2)0.006 (3)0.004 (2)0.008 (2)
C330.070 (5)0.109 (6)0.078 (5)0.017 (4)0.018 (4)0.005 (4)
C340.099 (6)0.089 (5)0.069 (4)0.030 (4)0.028 (4)0.008 (4)
C350.117 (6)0.056 (4)0.049 (3)0.016 (4)0.013 (3)0.001 (3)
C360.108 (5)0.053 (3)0.045 (3)0.000 (3)0.010 (3)0.008 (3)
C370.093 (5)0.096 (5)0.090 (5)−0.014 (4)−0.029 (4)0.000 (4)
N110.065 (3)0.041 (2)0.041 (2)−0.002 (2)−0.004 (2)0.0020 (17)
N120.065 (3)0.044 (2)0.047 (2)0.006 (2)0.003 (2)0.0008 (19)
N210.055 (2)0.034 (2)0.039 (2)0.0076 (17)−0.0045 (19)−0.0001 (17)
N220.107 (4)0.039 (2)0.049 (3)0.010 (2)−0.006 (2)−0.003 (2)
O10.126 (4)0.119 (4)0.085 (3)0.064 (4)−0.030 (3)−0.013 (3)
Cl10.0588 (8)0.0530 (8)0.0862 (10)−0.0017 (7)−0.0193 (7)0.0089 (7)
Cl20.0509 (7)0.0671 (9)0.0661 (8)0.0038 (7)−0.0010 (6)−0.0147 (7)
Pd10.0545 (2)0.0340 (2)0.0403 (2)0.00246 (17)−0.00455 (17)−0.00125 (16)
C11—N121.342 (6)C25—H25C0.9600
C11—C121.358 (8)C26—O11.202 (7)
C11—C141.501 (8)C26—N221.459 (7)
C12—C131.388 (7)C26—C311.475 (7)
C12—H120.9300C32—C311.389 (8)
C13—N111.340 (6)C32—C331.398 (8)
C13—C151.498 (8)C32—H320.9300
C14—H14A0.9600C31—C361.394 (8)
C14—H14B0.9600C33—C341.336 (10)
C14—H14C0.9600C33—H330.9300
C15—H15A0.9600C34—C351.449 (10)
C15—H15B0.9600C34—H340.9300
C15—H15C0.9600C35—C361.333 (8)
C21—C221.328 (9)C35—H350.9300
C21—N221.377 (7)C36—C371.529 (9)
C21—C241.501 (8)C37—H37B0.9600
C22—C231.398 (8)C37—H37C0.9600
C22—H220.9300C37—H37A0.9600
C23—N211.319 (6)N11—N121.350 (5)
C23—C251.503 (8)Pd1—N111.989 (4)
C24—H24A0.9600Pd1—N212.042 (4)
C24—H24B0.9600Pd1—Cl12.2981 (15)
C24—H24C0.9600Pd1—Cl22.3001 (15)
C25—H25A0.9600N12—H12A0.8600
C25—H25B0.9600N21—N221.359 (5)
N12—C11—C12106.2 (5)N22—C26—C31116.0 (5)
N12—C11—C14121.3 (5)C31—C32—C33119.4 (6)
C12—C11—C14132.5 (5)C31—C32—H32120.3
C11—C12—C13107.1 (5)C33—C32—H32120.3
C11—C12—H12126.5C32—C31—C36120.9 (5)
C13—C12—H12126.5C32—C31—C26117.0 (5)
N11—C13—C12109.3 (5)C36—C31—C26121.7 (5)
N11—C13—C15120.5 (5)C34—C33—C32119.6 (7)
C12—C13—C15130.1 (5)C34—C33—H33120.2
C11—C14—H14A109.5C32—C33—H33120.2
C11—C14—H14B109.5C33—C34—C35120.6 (6)
H14A—C14—H14B109.5C33—C34—H34119.7
C11—C14—H14C109.5C35—C34—H34119.7
H14A—C14—H14C109.5C36—C35—C34119.8 (6)
H14B—C14—H14C109.5C36—C35—H35120.1
C13—C15—H15A109.5C34—C35—H35120.1
C13—C15—H15B109.5C35—C36—C31119.6 (7)
H15A—C15—H15B109.5C35—C36—C37118.9 (6)
C13—C15—H15C109.5C31—C36—C37121.5 (6)
H15A—C15—H15C109.5C36—C37—H37B109.5
H15B—C15—H15C109.5C36—C37—H37C109.5
C22—C21—N22106.5 (5)H37B—C37—H37C109.5
C22—C21—C24131.2 (6)C36—C37—H37A109.5
N22—C21—C24122.2 (6)H37B—C37—H37A109.5
C21—C22—C23107.3 (5)H37C—C37—H37A109.5
C21—C22—H22126.3C13—N11—N12105.4 (4)
C23—C22—H22126.3C13—N11—Pd1133.6 (3)
N21—C23—C22110.0 (5)N12—N11—Pd1120.5 (3)
N21—C23—C25121.6 (5)C11—N12—N11112.0 (4)
C22—C23—C25128.4 (5)C11—N12—H12A124.0
C21—C24—H24A109.5N11—N12—H12A124.0
C21—C24—H24B109.5C23—N21—N22105.7 (4)
H24A—C24—H24B109.5C23—N21—Pd1127.7 (3)
C21—C24—H24C109.5N22—N21—Pd1126.6 (3)
H24A—C24—H24C109.5N21—N22—C21110.4 (4)
H24B—C24—H24C109.5N21—N22—C26123.3 (4)
C23—C25—H25A109.5C21—N22—C26125.8 (5)
C23—C25—H25B109.5N11—Pd1—N21174.88 (15)
H25A—C25—H25B109.5N11—Pd1—Cl188.39 (13)
C23—C25—H25C109.5N21—Pd1—Cl190.02 (12)
H25A—C25—H25C109.5N11—Pd1—Cl289.98 (13)
H25B—C25—H25C109.5N21—Pd1—Cl291.84 (12)
O1—C26—N22117.9 (5)Cl1—Pd1—Cl2176.71 (5)
O1—C26—C31125.4 (6)
N12—C11—C12—C13−0.2 (6)C14—C11—N12—N11180.0 (5)
C14—C11—C12—C13−179.9 (6)C13—N11—N12—C11−0.1 (6)
C11—C12—C13—N110.1 (7)Pd1—N11—N12—C11−173.1 (3)
C11—C12—C13—C15179.5 (7)C22—C23—N21—N22−4.3 (6)
N22—C21—C22—C23−2.1 (7)C25—C23—N21—N22176.5 (6)
C24—C21—C22—C23−179.4 (7)C22—C23—N21—Pd1175.7 (4)
C21—C22—C23—N214.1 (7)C25—C23—N21—Pd1−3.5 (8)
C21—C22—C23—C25−176.7 (7)C23—N21—N22—C213.0 (6)
C33—C32—C31—C36−0.2 (8)Pd1—N21—N22—C21−177.0 (4)
C33—C32—C31—C26−173.4 (6)C23—N21—N22—C26−168.9 (5)
O1—C26—C31—C32149.9 (7)Pd1—N21—N22—C2611.1 (7)
N22—C26—C31—C32−21.1 (7)C22—C21—N22—N21−0.5 (7)
O1—C26—C31—C36−23.3 (10)C24—C21—N22—N21177.0 (6)
N22—C26—C31—C36165.7 (5)C22—C21—N22—C26171.1 (6)
C31—C32—C33—C340.2 (10)C24—C21—N22—C26−11.3 (11)
C32—C33—C34—C35−0.9 (11)O1—C26—N22—N21125.6 (7)
C33—C34—C35—C361.7 (10)C31—C26—N22—N21−62.7 (7)
C34—C35—C36—C31−1.7 (9)O1—C26—N22—C21−45.1 (10)
C34—C35—C36—C37178.3 (6)C31—C26—N22—C21126.6 (6)
C32—C31—C36—C351.0 (8)C13—N11—Pd1—Cl1−79.2 (5)
C26—C31—C36—C35173.9 (5)N12—N11—Pd1—Cl191.4 (3)
C32—C31—C36—C37−179.0 (5)C13—N11—Pd1—Cl297.9 (5)
C26—C31—C36—C37−6.1 (8)N12—N11—Pd1—Cl2−91.5 (3)
C12—C13—N11—N120.0 (6)C23—N21—Pd1—Cl1−68.9 (4)
C15—C13—N11—N12−179.5 (6)N22—N21—Pd1—Cl1111.1 (4)
C12—C13—N11—Pd1171.6 (4)C23—N21—Pd1—Cl2113.8 (4)
C15—C13—N11—Pd1−7.9 (9)N22—N21—Pd1—Cl2−66.2 (4)
C12—C11—N12—N110.2 (6)
D—H···AD—HH···AD···AD—H···A
N12—H12A···Cl2i0.862.353.194 (4)169
Pd1—N111.989 (4)
Pd1—N212.042 (4)
Pd1—Cl12.2981 (15)
Pd1—Cl22.3001 (15)
N11—Pd1—N21174.88 (15)
N11—Pd1—Cl188.39 (13)
N21—Pd1—Cl190.02 (12)
N11—Pd1—Cl289.98 (13)
N21—Pd1—Cl291.84 (12)
Cl1—Pd1—Cl2176.71 (5)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N12—H12A⋯Cl2i0.862.353.194 (4)169

Symmetry code: (i) .

  3 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  New antitumor-active azole-bridged dinuclear platinum(II) complexes: synthesis, characterization, crystal structures, and cytotoxic studies.

Authors:  S Komeda; M Lutz; A L Spek; M Chikuma; J Reedijk
Journal:  Inorg Chem       Date:  2000-09-18       Impact factor: 5.165

3.  Trans-bis[3,5-bis(trifluoromethyl)-1H-pyrazole-kappaN2]dichloropalladium(II) monohydrate.

Authors:  Lara C Spencer; Ilia A Guzei; Stephen O Ojwach; James Darkwa
Journal:  Acta Crystallogr C       Date:  2006-08-23       Impact factor: 1.172
  3 in total
  1 in total

1.  Tetra-μ-acetato-κO:O'-bis-[(3,5-di-methyl-1H-pyrazole-κN)-copper(II)].

Authors:  Juanita van Wyk; Bernard Omondi; James Darkwa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27
  1 in total

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